Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α-Ketoamides and α-Ketotetrazoles

Christopher Foley, Arthur Shaw, Christopher Hulme

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A new postcondensation multicomponent reaction (MCR) methodology, comprising oxidative deaminations enabling access to multiple privileged carbonyl-containing scaffolds in two steps, is described. These protocols allow facile access to functionalized α-ketoamide and α-ketotetrazole small-molecule peptidomimetic-like building blocks from prototypical synthons with two points of diversity. Incorporation of chalcone and alkynyl moieties with further ring-forming reactions enables access to additional novel heterocyclic ring systems, including a unique and potentially highly pharmacologically relevant scaffold, a 1,2-selenazol-3(2H)-one.

Original languageEnglish (US)
Pages (from-to)2238-2241
Number of pages4
JournalOrganic Letters
Volume19
Issue number9
DOIs
StatePublished - May 5 2017

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Peptidomimetics
Chalcone
Deamination
Azides
Scaffolds
Oxidation
oxidation
rings
products
methodology
Molecules
molecules

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "A new postcondensation multicomponent reaction (MCR) methodology, comprising oxidative deaminations enabling access to multiple privileged carbonyl-containing scaffolds in two steps, is described. These protocols allow facile access to functionalized α-ketoamide and α-ketotetrazole small-molecule peptidomimetic-like building blocks from prototypical synthons with two points of diversity. Incorporation of chalcone and alkynyl moieties with further ring-forming reactions enables access to additional novel heterocyclic ring systems, including a unique and potentially highly pharmacologically relevant scaffold, a 1,2-selenazol-3(2H)-one.",
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